We insure small businesses and enable big dreams – not just for our customers, but for our people and communities too. With over 1,000,000 active insurance policies, we protect builders, bakers, landlords and more than 1,200 other trades.
We’re a technology company as well as one that sells insurance. That means we build, we fail, we learn and we improve. Through our global social impact strategy, called 'The Big Dreams Project’, we're working to help 10,000 small businesses start or grow by 2030.
Why not check out our advert on YouTube: Simply Business TV advert 2024: 'Simply the Best'.
Job CategoryProductPosition TypeTarget Openings1What Is the Opportunity?Imagine stepping into a role where you hold the keys to the front door of our digital growth engine. As our Senior Product Manager for customer acquisition and research, you’ll lead the top-of-funnel experience—crafting the very first impressions for small business owners as they land on our pages, research their insurance needs, and begin their journey with us.What makes this role different? You aren’t just managing a standard funnel; you are pioneering the next generation of online sales experiences. Operating in an agile, cross-functional value stream, you’ll have the license to experiment, obsess over conversion optimisation, and leverage emerging AI and Generative AI technologies to completely reimagine how complex products feel to the consumer. It’s the perfect blend of deep data strategy, customer empathy, and cutting-edge tech.Here’s what you’ll be doing:
Driving vision and roadmap: Own the discovery, delivery, and roadmap for our online sales journey, ensuring we constantly optimise our conversion flows and unlock new audiences.
Pioneering AI experiences: Proactively champion and integrate novel technologies like AI and GenAI to build highly personalised, flexible, and intuitive landing and research experiences.
Obsessing over the customer: Champion user-centered design to turn complex, misunderstood insurance products into a seamless, hassle-free online purchase journey.
Fostering a test-and-learn culture: Lead a "Build, Measure, Learn" environment, driving continuous experimentation and taking accountability for key conversion-to-purchase OKRs.
Collaborating across disciplines: Partner closely with engineering, data analytics, design, marketing, and insurance product teams to align everyone behind a shared, high-impact goal.
Balancing tech and business: Use your sharp commercial and technical judgment to make data-driven trade-offs, balancing delivery speed with high-quality user experiences.
We’re looking for someone who is:
A seasoned product expert: You have extensive experience navigating iterative product development—from early ideation and discovery to launch and optimisation—ideally within agile or value stream frameworks.
Tech-forward and AI-curious: You possess strong technological acumen and a genuine desire to leverage AI/GenAI frameworks to solve real-world user problems.
Data-driven and analytical: You live in the data, using tools like Amplitude, Looker, or Tableau to back up your decisions and shape a robust product strategy.
A natural collaborator and influencer: You can seamlessly unite cross-functional teams and diverse stakeholders around a singular, inspiring mission.
An inspirational leader: You lead by example, motivate your team through complex challenges, and know how to strike the perfect balance between design, technical, and commercial trade-offs.
Regulated industry savvy (a plus!): Previous experience in fintech or insurtech is great, but a deep commitment to translating customer pain points into brilliant UX is what truly matters.
(We know it's tough, but please try to avoid the confidence gap. You don't have to match all the bullet points above to be considered for this role.)
Be yourself at Simply Business
We encourage people of all different backgrounds and identities to apply. We are committed to maintaining an inclusive, supportive place for you to be you and do your very best work.
Ready to build the future of digital acquisition?If you are a product purist who loves clean UX, thrives on high-volume data experimentation, and wants to get your hands dirty with real-world AI implementation, we want to hear from you. We’re removing the jargon, breaking down the complexities of insurance, and scaling a growth engine that protects over 900,000 small businesses. Ready to own the front door? Apply today and let’s build something refreshing together.
What are the benefits of working at Simply Business:we offer a great work-life balance where workloads are manageable and everyone has the flexibility to work hybrid
on top of the 25 days annual leave (plus bank holidays), we offer the option to buy five more days of holiday with your flexible benefits
our flexible parental leave allows you to approach an important time how you want - with six months full pay to the primary caregiver and four weeks full pay if you're the secondary caregiver
our life event leave is an extra days leave every two years for those big moments in your life like moving house or your birthday. And our long-serving employees get a two week paid sabbatical after five years of service, then four weeks off after ten years of service
private medical insurance through BUPA, that covers any pre-existing condition is a core benefit. Plus a health cash plan that covers your everyday medical expenses
we offer a competitive salary based on your experience and the current market. Plus the potential to earn an annual bonus based on performance
access to tools to support your personal development on our dedicated learning platform. As well as support for your mental health with access to counselling
we match what you put into your pension up to five per cent. And pass on a tax-free sum that's four times your basic salary with our life assurance policy, with the option to increase it to ten times through our flexible benefit scheme
our salary sacrifice car scheme gives you the option to buy a brand new, fully insured, and maintained car for a convenient fixed monthly amount taken from your gross salary (after 6 months service)
our flexible benefits scheme gives you an allocated amount to use each year on benefits like critical illness cover, dental insurance, travel insurance, or a gym membership
Ready to join us and drive our success as a high-performing team? Apply today.
Employment PracticesSimply Business is committed to providing equality and opportunities for all employees and candidates considering a career with us. We offer a workplace where colleagues are treated with respect and dignity. We don’t (and won’t) discriminate either directly or indirectly on the grounds of race, colour, religion, belief, political opinion, disability, nationality, ethnic origin, sex, sexual orientation or relationship status at any stage of the hiring process or during the course of your employment.
Skills Required
- Extensive product management experience across discovery, delivery, and optimisation within agile or value stream frameworks
- Experience leading customer acquisition, conversion optimisation, and experimentation (Build-Measure-Learn, A/B testing) and owning conversion-to-purchase OKRs
- Practical experience integrating AI and Generative AI into product experiences
- Strong analytical skills with experience using Amplitude, Looker, Tableau, or similar analytics tools
- Proven ability to collaborate cross-functionally and influence stakeholders (engineering, data, design, marketing, product)
- Leadership experience motivating teams and making technical, design, and commercial trade-offs
- Experience in regulated industries such as fintech or insurtech
What the Team is Saying
Simply Business Compensation & Benefits Highlights
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Leave & Time Off Breadth — Time off is notably extensive, with 25 vacation days, 10 sick days, multiple holidays, and paid sabbaticals after long service. Feedback suggests this level is generous for the U.S. market.
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Retirement Support — Retirement support includes a 401(k) with a 100% employer match up to 5%. Feedback suggests this match compares favorably to many mid‑market employers.
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Parental & Family Support — Family benefits include generous parental leave, an on‑site mother’s room, and childcare tuition discounts. Feedback suggests these supports complement core coverage to strengthen total rewards.
Simply Business Insights
What We Do
Simply Business is the leading digital insurance marketplace dedicated to the success of small businesses. Our mission is to take the hassle out of buying insurance by offering simplicity, choice, and value to business owners. We connect our customers with top-rated insurers and policy recommendations tailored to their specific business needs and budget. We have nearly 20 years of experience supporting small businesses, with over 1 million customers worldwide. Founded in the U.K. in 2005, Simply Business revolutionized how small businesses find insurance, making it accessible and affordable. We then saw a similar need in the United States. So in 2017, we launched Simply Business in the U.S.. Today, our team sits across offices in Boston in the U.S., as well as in London and Northampton in the U.K., showcasing our innovation at scale and dedication to serving the backbone of our economies. Simply Business is more than our name. It’s how we approach small business insurance.
Why Work With Us
Here at Simply Business we have five core values that we uphold in everything that we do: Learning, Empowerment, Authenticity, Pioneering, and Simplicity. Utilizing these values and embedding them into our culture makes SB a unique and great place to work, a place where every person is valued, a place where we get things done and have fun doing so.
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Simply Business Teams
Simply Business Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We offer our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives.
